


Happy New Years....Again...Again...And Again

by Negative_Citadel



Category: Milo Murphy's Law
Genre: Groundhog Day, M/M, New Years, New York City, Zack trying to ask Milo out, just wholesome
Language: English
Status: In-Progress
Published: 2021-02-14
Updated: 2021-02-14
Packaged: 2021-03-15 09:01:58
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,186
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29433558
Author URL: https://archiveofourown.org/users/Negative_Citadel/pseuds/Negative_Citadel
Summary: Milo, Melissa, and Zack head to New York to celebrate New Year's and watch the ball drop. Meanwhile, Zack is hoping to confront Milo about his crush on him. Suddenly, it feels like New Year's Eve won't end.(Unoriginal groundhog day nonsense ensues)
Relationships: Milo Murphy/Zack Underwood
Kudos: 6





	Happy New Years....Again...Again...And Again

**Author's Note:**

> This was originally supposed to be a short oneshot, but I went kinda crazy. I'll get the second part out soon..ish. I enjoy rotating stories I'm working on and this alone took me three or four days to work on. I'll probably draw something for the next chapter if I somehow learn how to draw humans lol.

“Today’s the day,” Milo excitedly exclaimed as he tossed a pillow at Zack, causing him to wake up. Milo ran to the dresser across their room in the hotel and pulled out some clothes to change into. “Are you ready for 2023?” He asked his friends playfully as he snuck into the bathroom to change.

Melissa yawned as she laid in the adjacent bed from Zack. She was not a morning person. “Seems like Milo is already excited.” 

“I know right?” Zack chuckled as he got up. He heard something break in the bathroom. “Milo, you alright in there?” He shouted, still only half awake.

“Yeah, just give me a minute,” Milo called out. It didn’t take him long to slide out of the bathroom. “This is a very fancy hotel,” he commented as he looked into the living room portion of it. He grabbed a soda from the small mini cooler by the tv. He drank it with a big grin on his face. “What are you guys thinking of doing? I don’t think the party starts until six at night so we have plenty of time to kill...but I really, really want to see the ball drop so we can’t stay at the party all night.”

Zack grabbed his clothes and left for his turn to get dressed in the bathroom. “You guys can brainstorm without me.”

“Do you have any ideas?” Melissa shrugged as she turned to Milo.

Milo pulled back the curtains and peered through the window of the hotel. They had an amazing view of New York City. The drive might’ve been extremely long, but they managed to make it all the way to Manhattan in one piece. Milo was able to see Melissa’s poor, beat up station wagon in the parking lot. Murphy’s Law sure did a number on it.

Milo pulled out a pamphlet about New York City from his backpack. “Let’s see,” he mumbled to himself as he eyed the pamphlet. “Looks like there’s a lot to do around the Rockefeller Center.” He gasped as his eyes glowed with excitement. “Let’s go ice skating - I’ve always wanted to go ice skating!”

“Are you sure that’s really a good idea?” Zack asked as he left the bathroom and sat on the bed. “We barely made it here in one piece.”

“Maybe we should just visit central park,” Melissa suggested before leaving to change into her clothes. “Let’s play this as safe as we can, alright?”

“Well,” Milo bit his tongue. “I thought it’d fun to go ice skating.”

“Do you even know how to ice skate?” Zack questioned in a somewhat condescending tone. It didn’t seem to bother Milo.

“No, but that’s what would make it fun! I’d love to learn one new skill before the year is over,” Milo stated with a big grin on his face. He put the pamphlet away in his backpack and sat beside Zack. “Have you thought about your New Year’s resolution yet?”

Zack nodded. “I have, but I’m not telling anyone until after the clock strikes midnight. I want to see that ball drop before I set anything in stone.”

Melissa stepped out. “Are we all set to go?”

The three left the hotel room. Melissa shut the door behind them. Zack tugged on the door to make sure it was locked but it opened immediately. Melissa slammed the door then tried to open it. It was locked and the three of them walked to the elevator. Melissa pressed the button to call it.

“Are you sure it’s a good idea to take the elevator with Milo?” Zack whispered in Melissa’s ear as Milo patiently waited for the elevator to come up.

The elevator had finally arrived, but the doors would not open. Melissa pressed the button again, nothing happened. “Looks like we broke the elevator before we even go on it.” She shrugged and followed Milo to the stairs. They all bolted down eight floors of stairs. By the time they got to the bottom, they were all panting. 

They walked out of the hotel and boarded a bus. They were packed in tight with strangers like a pack of sardines. Milo was pressed up against his two friends as they waited for their stop. Once the bus stopped by central park, the three hopped off, going into the park. They walked down to the Balto statue. 

“Why’s there a statue of a dog?” Melissa asked.

“That’s Balto,” Milo began rambling about the history of the dog that delivered vaccines. Zack and Melissa began tuning him out as they looked around. He seemed to drone on for what felt like hours. His friends were happy to see him so excited, but they were ready to go. They yanked Milo backwards as a tree toppled over. “Thanks guys, I got a little carried away.” 

They continued down the park together. Milo walked ahead of them, talking about New York City and raving about the park. “When are you going to tell him?” Melissa said quietly to Zack as they slowly followed behind Milo.

Zack shook his head. “I don’t think it’s a good idea too.”

“Why? This seems like the perfect place to do so,” she murmured as they kept walking. “You can’t hide this from Milo forever. Eventually, he’s going to find someone else. I mean, what if he gets back together with Amanda?”

“Don’t even joke about that,” Zack grumbled with his hands in his pockets.

Milo turned his head to see Zack’s frustrated facial expression. “What’s wrong, Zack?” He took two steps back as a car’s tire bounced past him.

“Nothing,” Zack growled as he looked around. He pulled out his phone to check the time. “Maybe we should go to that party already. It’s almost six.”

“Good idea.”

The three rushed back to the hotel, hitting a fast food joint for a quick meal on the way. They went to the convention hall and were greeted by loud music. A light fell from the ceiling as they passed through. Melissa elbowed Zack’s back before heading towards a buffet table. Zack sighed as he watched Milo’s terrible dance moves.

Zack joined Milo, getting closer and closer as a large crowd filled the room. “Milo, I forgot to ask. What was your New Year’s resolution?”

“I can’t hear you over this music,” Milo shouted as he stopped dancing. The two walked out into the hotel lobby. They took a seat nearby the elevator. “What were you trying to say?”

Zack repeated himself. “What was your New Year’s resolution?” 

Milo shrugged. “I actually haven’t thought of one yet.” He paused as he noticed the frown on Zack’s face. “Zack, is something bothering you? You’ve been acting really strange.”

“I don’t know how to say this,” Zack itched the back of his shoulder as he looked away. Milo reassured him, telling him that he could tell him anything. Zack’s eyes returned to Milo’s. “I guess I minus well get mine over with now.”

“What do you mean?”

Zack looked down at the floor. “I was hoping to find love.”

“That won’t be hard for you,” Milo told him. “I mean, you were in a boy band! What girl wouldn’t want to date you?”

“Right…” Zack sighed. “When should we leave for the ball drop?”

“We just got here.”

“Yeah, but we probably want to get there early so Murphy’s Law doesn’t block our way,” Zack growled.

“Good point, I’ll go grab Melissa.” 

The three got together and began heading to times square. The area was packed and none of them could see anything. The crowds were massive and congested. The three squeezed through the crowd, trying to get a better view but all they could see was the hoard of people around them.

"I can't see anything," Zack moaned as he wiggled out of the crowd.

Mill sighed. "I can't either. Maybe we should've gone earlier."

"Maybe you two should have your own private New Years," Melissa suggested with a cheeky smile. 

"Why not the three of us?" Milo asked.

"I'll meet you guys back at the hotel," she told him. She winked at Zack. "I think you two should have some alone time. I'm all Murphy'd out right now."

“If you’re sure,” Milo murmured.

“We can do anything you’d want,” Zack offered to Milo with a big grin on his face.

Milo's eyes lit up. "Let's go ice skating!"

Zack and Milo left the area and headed to the Rockefeller plaza. "Are you sure you want to do this?" Zack asked as nervously waited for something to go wrong. "Not much has happened today."

"Murphy's Law is unpredictable," Milo shrugged as he put ice skates on. He handed a pair to Zack.

"Have you been carrying these in your backpack the whole time?"

"Yeah," Milo said as he got closer to the ice rink. His legs wobbled as he clung to the wall. He waited for Zack to join him.

Zack grabbed Milo's shoulders. "You need to stand upright and balance. If you think you're going to fall, then you will." He reached an arm behind Milo's back, keeping him standing up straight.

"Thanks, Zack."

Zack held Milo’s hand as they skated together. He nervously scanned the area, waiting for something to go wrong. He looked at Milo and smiled. “Looks like Murphy’s Law is giving you a break for once!”

“I wouldn’t say that,” Milo shrugged as he skated alongside Zack. His hand clenched Zack’s as he struggled to balance. “It can be pretty unpredictable at times.”

“Was there anything else you wanted to try?” Zack asked.

“Well, I’m kinda disappointed we didn’t get to see the ball drop,” Milo murmured as his legs shaked a little on the ice. Zack wrapped an arm around him to stabilize him. “It is pretty cold out, maybe we should just head back to the hotel and grab a pizza.”

The two left to catch a bus. As they took their seats, they noticed two familiar faces. Milo waved, “Hey, Cavendish and Dakota, what’re you guys doing here?”

“It’s kind of a long story,” Dakota mumbled as he messed with a strange device in his hands while Cavendish was quietly watching him. “What are you guys doing?”

“Well, we originally wanted to see the ball drop, but that didn’t work out,” Milo told the two about their day so far. Zack watched the cars pass by the slow bus as it headed for the hotel. 

Suddenly, the bus hit a large bump and the device in Dakota’s hands slipped out of his grasp and fell onto the floor, shattering in seconds. Cavendish glared at him. “Look what you just did!”

“Yeah, yeah, like that was my fault,” Dakota shrugged as he rolled his eyes. “We’ll get it fixed. It’s not a big deal.”

“What was it?” Zack asked curiously.

“Something I stole from Brick and Savannah,” Dakota said quietly as he began collecting all the pieces off the floor. He shoved them into his track suit’s pockets. He smiled nervously as Cavendish glared at him.

“Something that you shouldn’t have stolen!” Cavendish scolded him. “Do you have any idea what you’ve done?”

The two continued to argue as Zack and Milo left the bus anxiously. They rushed up the flight of stairs to their hotel room. The higher they got, the slower they ran until they were practically crawling. Milo pushed open the door before toppling onto the bed. He breathed heavily as he watched Zack lay beside him.

“Zack...we...forgot...to…”

“We forgot the pizza,” Zack groaned.

“Exactly.”

Zack sighed and looked around the hotel for a fire extinguisher. There were only sprinklers on the ceiling. “I don’t want to risk a fire setting off the sprinklers,” he told Milo as he sat up. “I’ll just text Melissa to grab a pizza while she’s out.”

“Sounds good.”

Zack texted Melissa, then put his phone down on the nightstand. He looked down at Milo, who laid, stretched out on the bed. He looked up at the clock on the wall, seeing it wasn’t far from midnight. “Milo, there’s something I really want to tell you.”

“What is it, Zack?”

“Here goes nothing,” Zack mumbled to himself as he laid back down to face Milo. “I like you, Milo.”

“I like you too, Zack,” Milo said with an eager smile. “You’re the best friend-”   
  


“No, Milo, I mean, I really like you.”

“I really like-”

“No, I mean I…” Zack groaned. “Milo, I like you as more than just a friend.”

Suddenly, it clicked and the boy in the sweater vest was silent for a second. “Oh.”

“Yeah.”

“You…”

“Yeah.”

The room was silent for almost an entire minute. Milo’s face became red as he turned away from Zack. “Well, this is awkward.”

“Is that really your only response?” Zack growled as he stood off the bed. “You won’t even look me in the eyes to reject me?”

Milo sighed as he sat on the bed. He looked up at Zack. “I’m not rejecting you-”

“You’re not?”

“No,” Milo’s face was still as red as ever. “I just didn’t think anyone would like me like that...after Amanda dumped me.”

“Milo, that was a long time ago.”

“Well, nobody ever asked me out since…" Milo told him with wet eyes. His frown broke as he meekly smiled. “Nobody has till now.”

Zack sat down and wrapped an arm around Milo. Murphy leaned onto his shoulder. He looked up at the clock and pointed. "Milo, it's almost midnight."

Milo smiled as he held onto Zack. "Did you figure out your New Year's resolution?"

"I've already done it." He was no longer interested in the ticking clock above them as it had struck midnight.

The two tiredly laid on the bed. Milo pulled a blanket over himself and let out a long yawn. "I wonder where Melissa is."

Zack shrugged as he let out his own yawn. "She can just lay the pizza in the mini fridge."

The two boys bundled up with blankets before closing their eyes. Zack held Milo close as he slept. He yawned as he heard someone calling him. Stretching out his body, Zack opened his eyes. He looked down to see Milo comfortably laying his head on his chest, still fast asleep.

"Looks like you got what you wanted before you even told him," Melissa chuckled as she pulled the hotel blinds to reveal the sunlight. "I can't believe you guys are sleeping in." She picked up Milo's bag and looked through it, grabbing the New York City pamphlet. "Alright, what do we want to do to pass the time while we're waiting for midnight?"

Zack gave her a weird look. "What do you mean?"

"Well, I know Milo wants to see the ball drop, but I wasn't sure if there was anything we wanted to try to do anything else first." She quickly read through the pamphlet. "I wasn't sure if there was a place you wanted to ask Milo out at."

"You do realize it's already January first, right?"

Melissa glared at him. "Zack, what are you talking about?"

"We missed the ball drop because of the crowds, remember?"

"Zack, I have no clue what you're talking about." She sighed as she pulled out her phone and handed it to him, showing him the date. "It's New Year's Eve. You must've had a dream or something."

"That can't be possible-" Zack tried to sit up, but Milo pulled him back down.

"Five more minutes," Milo purred as he clung to Zack.

"Milo," Zack groaned and pushed him away so that he could get up. "Milo, wake up, already."

Milo yawned. "What is it?" His eyes were only half open. "Oh, hey, Melissa."

"Tell her about last night."

Milo stretched his legs onto the bed. "Zack and I went ice skating for a while. Then we came back here and right before midnight, Zack…" He began to blush as he sat up. "He asked me out...kind of. I don't remember the details, I was tired."

"You guys stayed up till midnight last night?" Melissa asked. "You're going to fall asleep before you can see the ball drop!"

"I'm pretty sure the ball already dropped," Milo commented as he looked outside. He turned to the clock on the wall, or, where it used to be. Laying on the floor was a broken clock. “What time is it?” Melissa showed him her phone. “That can’t be right-”

“What has gotten into you guys?” Melissa sneered. “It’s almost the afternoon! We should really head out and do something.”

“Let’s arrive at times square early, so we can see the ball drop,” Zack suggested and the two others agree. Together, they left the hotel room. Melissa shut the door behind them. Zack opened it, then slammed it shut, making sure it was properly locked again. Melissa walked over to the elevator while Zack steered Milo towards the door to the stairs. “The elevator doors wouldn’t open last time,” he shouted to her before walking down the stairs with Milo. It wasn’t long before Melissa followed.

They boarded the same busy bus they did before. “I’m beginning to think you guys really did experience New Years already,” Melissa crossed her arms as she sat beside Milo.

Milo shrugged. “It is possible, but highly unlikely, that Zack and I had the same dream.”

“That’s why I want to go to Times Square and wait for the ball,” Zack told her, ignoring Milo’s comment. “Last night, we missed it because of the crowds. If we get there early enough then-”

“Why do you guys remember last night and I don’t?” Melissa immediately asked, cutting off Zack as the bus hit a bump in the road. 

“I honestly have no clue,” Zack said. “I don’t even know why the day repeated.”

The three walked to Times Square and waited anxiously. Melissa pulled out her phone to play some mobile games. Zack and Milo began discussing everything that happened last night, trying to figure out what might have caused the way to repeat itself. “Wait, remember when we were on the bus and Dakota dropped that sphere?”   
  


“You guys ran into Dakota?” Melissa asked, looking up from her phone.

The two boys nodded. “...and Cavendish,” Zack added.

Milo gasped. “Maybe if we prevent that sphere from breaking-”

“How do we expect to find Dakota and Cavendish in this big city?” Zack questioned.

“Milo, you don’t happen to have their phone number, do you?”

“I have Dakota’s!” Milo pulled out his phone and held it up, only for a crow to grab it and fly away with it. He placed his backpack onto the sidewalk. “Spare...Spare,” he rummaged through his bag until he found another phone. “There we go.” He dialed Dakota’s number, only to go to voicemail. “He doesn’t usually answer,” Milo commented, disappointedly. 

“I guess we’re doing this the hard way,” Melissa rolled her eyes as she pointed to a bus. “Let’s split up and hit every bus, subway, and taxi we can find.” 


End file.
